Triphenylphosphine → HCID 18460571, compound

HRID 2303360Notes

Reaction equation

HRID 2303360 reaction equation
O[CH2:2][CH2:3][N:4]([CH2:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]([C:28]2[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=2)[CH:23]=1)[C:5](=[O:20])[CH2:6][NH:7][S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18])(=[O:10])=[O:9].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[N+:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[S:8]([N:7]1[CH2:2][CH2:3][N:4]([CH2:21][C:22]2[CH:27]=[CH:26][N:25]=[C:24]([C:28]3[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=3)[CH:23]=2)[C:5](=[O:20])[CH2:6]1)(=[O:10])=[O:9])([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 86758400HCID 86758400, compound

Product 1

HCID 18460571HCID 18460571, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(2-Hydroxyethyl)-N-[[2-(3,4,5-trimethoxy-phenyl)pyridin-4-yl]methyl]-Nα-(2-nitrobenzenesulfonyl)-glycine amide (2.22 g) was dissolved in THF, and to the solution triphenylphosphine (1.55 g) was added. DEAD (1.03 g) was slowly added to the mixture at room temperature, and the resultant mixture was stirred overnight at room temperature under an argon atmosphere. After the reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the residue. The mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate) to obtain the title compound.

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure, ethyl acetate
  2. additionwas added to the residue
  3. washThe mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-6b28139176934239b1e5f4d7df4c5616
Source dataset
uspto-grants-2002_08
Patent number
US06432957B1

Reaction notes

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